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$1,099,000
2 Beds ⋅ 3 Baths ⋅ 1004449 MLS
Welcome to this beautifully situated townhouse in the highly desirable Riverwoods community, where tranquil woodland views and thoughtfully designed living spaces create the perfect retreat. Nestled against a picturesque backdrop of mature trees and a gently flowing stream, this home offers both privacy and natural beauty in an exceptional setting. The sun-filled eat-in kitchen is as inviting as it is functional, featuring granite countertops, a gas stove, abundant cabinetry, and plenty of space for casual dining. Just beyond, the elegant formal dining room is framed by stunning triple floor-to-ceiling windows that bring the outdoors in and fill the space with natural light. The gracious living room is equally impressive, highlighted by detailed dentil moldings, a classic wood-burning fireplace with a handsome wood mantel, and sliding doors that open to a spacious deck overlooking the serene wooded landscape—an ideal spot for morning coffee, outdoor dining, or simply unwinding in nature. As you ascend to the second floor, a sunlit hallway lined with three oversized windows creates a bright and airy ambiance throughout the home. The expansive primary suite is a true sanctuary, featuring soaring cathedral ceilings, a generous walk-in closet, and a charming Juliet balcony with peaceful views of the private woods below. The luxurious primary bath offers a double vanity, a relaxing soaking tub, and a separate stall shower for a spa-like experience. A second spacious bedroom with its own ensuite bath provides comfort and privacy for family or guests, while the conveniently located laundry area on the upper landing adds everyday ease. The walk-out lower level offers exceptional flexibility, with a large family room perfect for gatherings, movie nights, or recreation. An additional versatile room can easily serve as a home office, gym, or guest space, complemented by a convenient half bath. A dedicated storage room and utility area complete this well-designed lower level. Combining elegant architectural details, generous living spaces, and a spectacular natural setting, this exceptional Riverwoods home offers comfort, charm, and a lifestyle of relaxed sophistication.

4 Annes Wood Lane, Mount Kisco
$3,100,000
5 Beds ⋅ 6 Baths ⋅ 990281 MLS
Privately gated and masterfully crafted, this exceptional custom brick estate is a showcase of timeless elegance and grand-scale living, nestled on over two acres in the heart of Chappaqua. Beyond the cobblestone apron and curbing, a sweeping driveway leads to a residence designed for both luxury and comfort, boasting soaring 10-foot ceilings, four stately fireplaces, exquisite architectural detail, and refined finishes throughout. Enter through a breathtaking grand foyer, where gleaming hardwood floors with intricate wood inlay medallion set the tone, and a dramatic three-story suspended spiral staircase anchors the home in architectural splendor. The main level is ideal for entertaining, offering a formal living room, formal dining room, an expansive family room with a custom bar, and seamless access to a private bluestone patio, perfect for indoor-outdoor gatherings. The chef’s kitchen is a culinary masterpiece, featuring high-end appliances, breakfast area, butler’s pantry, and dual access points to the patio. A main-floor guest/au pair suite, private office or den, and powder room complete the level. Upstairs, the serene Master Suite is a retreat unto itself, complete with a sitting area, dual walk-in closets, and a spa-like marble bath with heated towel racks, dual vanities, clawfoot soaking tub, and an oversized glass shower. Three additional generously-sized bedrooms, one with an ensuite, and a full hall bath, along with a dedicated laundry room, offer both comfort and convenience. The third floor adds a spacious game and media room, while the walk-out lower level features a gym, mudroom, recreation space, sitting area, and access to the beautifully landscaped backyard. Outside, enjoy artisan stonework, multiple patios, a gazebo, hot tub, built-in BBQ station, and lush, level grounds ideal for entertaining and play. Three heated garages, including an electric vehicle charging station, complete this extraordinary masterpiece with modern convenience and sophistication. Located just minutes from Chappaqua’s charming village center, award-winning schools, fine dining, shopping, Mt. Kisco Country Club, Metro North, and major highways. This is a a rare opportunity to own one of Chappaqua’s most distinguished estates, an architectural triumph of timeless sophistication and commanding presence, set within one of Westchester’s most coveted communities.

2 Heathcote Drive, Mount Kisco
$1,998,999
4 Beds ⋅ 4 Baths ⋅ 1011189 MLS
Nestled on over an acre of beautifully landscaped grounds in the highly sought-after Chappaqua School District, this exceptional residence offers a rare blend of privacy, craftsmanship, and versatility. Behind a gated entrance, mature specimen plantings, expansive lawns, and a tranquil natural setting create a true private retreat just minutes from downtown Chappaqua and Metro-North. Thoughtfully improved throughout the years, the home features cedar siding, Anderson windows and sliding doors, custom hardwood flooring with intricate inlay detail, reinforced structural beams, remote-controlled skylights, and numerous mechanical upgrades. Dramatic ceilings, walls of windows, and sun-drenched living spaces create an inviting atmosphere designed for both everyday living and entertaining. The eat-in kitchen is appointed with custom cabinetry, premium stainless steel appliances, a center island, and seamless access to the outdoor deck. Formal and informal living spaces flow effortlessly throughout the main level, highlighted by a dramatic living room with soaring ceilings, oversized windows, and a marble fireplace. The luxurious primary suite serves as a private retreat featuring custom California Closets and a stunning spa-inspired bath with a freestanding soaking tub, oversized glass-enclosed shower with body jets and bench seating, custom mahogany detailing, designer lighting, and exceptional finishes throughout. Renovated bathrooms throughout the home showcase custom tilework, premium fixtures, and thoughtful spa designs. Additional highlights include California Closets throughout, intercom and surround sound systems, smart gate access, surveillance cameras, irrigation system, renovated garage, and a charming detached storage shed. Outdoor living is equally impressive with expansive decking, a remote-controlled SunSetter awning, and peaceful grounds designed for entertaining and relaxation. A truly special offering combining privacy, quality craftsmanship, modern conveniences, and exceptional flexibility in one of Westchester County's most desirable communities.

4 Old House Lane, Chappaqua
$2,499,000
3 Beds ⋅ 4 Baths ⋅ 973551 MLS
Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods, this exceptional luxury Colonial blends timeless architecture, designer finishes, and an unmatched indoor-outdoor lifestyle within the award-winning Chappaqua school district. Privately positioned against acres of preserved land, this premier Westchester County property offers both tranquility and convenience, just minutes to Metro North, downtown Chappaqua, and Chappaqua Crossing featuring Whole Foods Market and Life Time. Living like a 5-bedroom home, this luxury home for sale in Chappaqua showcases exceptional craftsmanship throughout with Juliet balconies, copper-topped cupolas, Belgian block-lined driveways, soaring ceilings, custom millwork, and walls of glass that flood the interiors with natural light. A dramatic curved staircase welcomes you into elegant yet comfortable living spaces designed for both everyday living and sophisticated entertaining. The chef’s kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, and European mosaic tilework, seamlessly connecting to the formal and casual gathering spaces. Highlights include a sophisticated library with gas fireplace, a stunning vaulted family room, and an impressive entertainment lounge with a wood-burning fireplace, wet bar, Viking wine refrigerator, and custom built-ins. The luxurious primary suite offers a gas fireplace, oversized dressing room, and spa-inspired bath, delivering the ultimate private retreat. Outside, the property lives like a private resort with a heated saltwater pool, outdoor fireplace, expansive patios, built-in grill, fire pit, poolside grotto with shower and changing area, gazebos, and a half basketball court with spotlighting. This exceptional Chappaqua estate offers luxury living, privacy, and resort-style amenities in one of Westchester’s most sought-after communities, known for top-rated schools, vibrant downtown, and easy NYC commute. A rare opportunity to experience estate-style living and the quintessential Chappaqua lifestyle at its finest.

33 Greenbriar Drive, Chappaqua
$1,590,000
3 Beds ⋅ 4 Baths ⋅ 984583 MLS
Welcome to this sophisticated carriage home at 17 Lila Lane, offering a rare blend of contemporary luxury and maintenance-free living within the prestigious Chappaqua Crossing community. The thoughtfully designed layout is anchored by a gorgeous chef’s kitchen, featuring a large center island with ample seating and a premium JennAir appliance package. Equally enticing is the coveted first-floor primary suite, providing a serene sanctuary with a spa-inspired ensuite bathroom and an expansive walk-in closet. The second level serves as a versatile retreat, home to a spacious second bedroom, a dedicated home office/bedroom, an inviting sitting area, and a gorgeous private terrace. Additional living space abounds in the fully finished lower level, perfectly suited for a high-end home gym and a cozy media den, while the attached two-car garage comes equipped with an EV charging station for modern convenience. Residents enjoy an unparalleled "village within a village" lifestyle defined by sprawling green space and scenic walking trails, with exclusive access to a luxury clubhouse and sparkling pool. Situated in the heart of Chappaqua, this residence is just steps from Whole Foods, Life Time Fitness, delicious restaurants, and offers the convenience of a private community shuttle to the Metro-North for a seamless commute to Manhattan.

17 Lila Lane, Chappaqua
$4,500,000
5 Beds ⋅ 7 Baths ⋅ 950756 MLS
1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth. Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite. Set on more than four exceptionally private acres, the grounds unfold as a true outdoor sanctuary, featuring a beautiful pool and spa (32x20), refined pergola terraces ideal for entertaining, and a private tennis court. From its commanding hilltop position, the estate delivers an unparalleled sense of privacy, security, and timeless elegance. Welcome home!

150 Old Farm Road N, Chappaqua

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.